Catalytic umpolung allylation of aldehydes by π-allylpalladium complexes containing bidentate N-heterocyclic carbene ligands

被引:64
|
作者
Barczak, Nicholas T. [1 ]
Grote, Robin E. [1 ]
Jarvo, Elizabeth R. [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
PALLADIUM COMPLEXES; ELECTROPHILIC SUBSTITUTION; MECHANISM; REACTIVITY; ALCOHOLS;
D O I
10.1021/om700605y
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of pi-allylpalladium complexes with neutral monodentate and bidentate ligands were prepared and examined for their ability to undergo stoichiometric umpolung allylation reactions with benzaldehyde. Neutral bidentate N-heterocyclic carbene ligands promote nucleophilic attack. Catalytic allylation reactions of aromatic and aliphatic aldehydes are reported.
引用
收藏
页码:4863 / 4865
页数:3
相关论文
共 50 条
  • [41] Methanol Dehydrogenation by Iridium N-Heterocyclic Carbene Complexes
    Campos, Jesus
    Sharninghausen, Liam S.
    Manas, Michael G.
    Crabtree, Robert H.
    INORGANIC CHEMISTRY, 2015, 54 (11) : 5079 - 5084
  • [42] Ruthenium(II) complexes bearing pyridine-functionalized N-heterocyclic carbene ligands: Synthesis, structure and catalytic application over amide synthesis
    Nirmala, Muthukumaran
    Viswanathamurthi, Periasamy
    JOURNAL OF CHEMICAL SCIENCES, 2016, 128 (11) : 1725 - 1735
  • [43] Tunable iridium catalyst designs with bidentate N-heterocyclic carbene ligands for SABRE hyperpolarization of sterically hindered substrates
    Pham, Pierce
    Hilty, Christian
    CHEMICAL COMMUNICATIONS, 2020, 56 (98) : 15466 - 15469
  • [44] Dinuclear N-heterocyclic carbene copper(I) complexes
    Trose, Michael
    Nahra, Fady
    Cazin, Catherine S. J.
    COORDINATION CHEMISTRY REVIEWS, 2018, 355 : 380 - 403
  • [45] On the Bonding in N-Heterocyclic Carbene Complexes of Germanium(II)
    Ruddy, Adam J.
    Rupar, Paul A.
    Bladek, Kamila J.
    Allan, Christopher J.
    Avery, Jessica C.
    Baines, Kim M.
    ORGANOMETALLICS, 2010, 29 (06) : 1362 - 1367
  • [46] N-Heterocyclic Carbene Iron Silyl Hydride Complexes
    Quintero-Duque, Samuel
    Li, Haoquan
    Castro, Luis C. Misal
    Dorcet, Vincent
    Roisnel, Thierry
    Clot, Eric
    Grellier, Mary
    Sortais, Jean-Baptiste
    Darcel, Christophe
    ISRAEL JOURNAL OF CHEMISTRY, 2017, 57 (12) : 1216 - 1221
  • [47] A Cationic N-Heterocyclic Carbene Containing an Ammonium Moiety
    Ruamps, Mirko
    Lugan, Noel
    Cesar, Vincent
    ORGANOMETALLICS, 2017, 36 (05) : 1049 - 1055
  • [48] Dioxygen adducts of rhodium N-heterocyclic carbene complexes
    Keske, Eric C.
    Zenkina, Olena V.
    Asadi, Ali
    Sun, Hongsui
    Praetorius, Jeremy M.
    Allen, Daryl P.
    Covelli, Danielle
    Patrick, Brian O.
    Wang, Ruiyao
    Kennepohl, Pierre
    James, Brian R.
    Crudden, Cathleen M.
    DALTON TRANSACTIONS, 2013, 42 (20) : 7414 - 7423
  • [49] N-Heterocyclic Carbene Complexes of Cp*-Aluminum Triflate
    Wang, Chen-Hao
    Lin, Ya-Fan
    Tseng, Hsi-Ching
    Lee, Gene-Shiang
    Peng, Shie-Ming
    Chiu, Ching-Wen
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2018, (20-21) : 2232 - 2236
  • [50] F-Block N-Heterocyclic Carbene Complexes
    Arnold, Polly L.
    Casely, Ian J.
    CHEMICAL REVIEWS, 2009, 109 (08) : 3599 - 3611